emivirine

CHEBI:44143 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. A non-nucleoside inhibitor of HIV-1 reverse transcriptase, emivirine was an unsuccessful experimental agent for the treatment of HIV. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:38337

Chemical structure

Computed structure properties
Molecular formula	C17H22N2O3
Charge	0
Average mass	302.374 Da
Monoisotopic mass	302.16304 Da
Source	ChEBI
InChIKey	MLILORUFDVLTSP-UHFFFAOYSA-N

SMILES

CCOCn1c(Cc2ccccc2)c(C(C)C)c(=O)nc1=O

InChI

InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

Also called

Coactinon (BRAND_NAME)— chebi
6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione (EXACT_SYNONYM)— chebi
1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione (EXACT_SYNONYM)— chebi
6-BENZYL-1-ETHOXYMETHYL-5-ISOPROPYL URACIL (EXACT_SYNONYM)— chebi
6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil (EXACT_SYNONYM)— chebi
MKC-442 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:149950-60-7
pdb-ccd:MKC
reaxys:7340168

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

kegg.drug:D01055

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral drug CHEBI:36044
HIV-1 reverse transcriptase inhibitor CHEBI:53756

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:44143`	emivirine	`antibioticmech:chebi-e98107dd91`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Gag-Pol polyprotein [588-1027]/[588-1147] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2849` `assay 429_1` `monomer 2337`	`PMID:11472208`
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2930` `assay 431_1` `monomer 2337`	`PMID:10052969`
IC50	40 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3042` `assay 440_1` `monomer 2337`	`PMID:14761194`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	REVIEWED

PMID:11472208 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10052969 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:14761194 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (emivirine) · CultureMech · NaturalProductMech · PathwayMech · TraitMech